Cottage and short-term rentals in Tobermory

Tobermory is really two harbours wearing one name. Little Tub is the busy one, where the ferry and the tour boats leave from and where you'll find most of the restaurants and shops. Big Tub, a short walk away, is quieter and holds the town's best-kept secret: two century-old shipwrecks, the Sweepstakes and the City of Grand Rapids, sitting in water so clear you can see their outlines from shore without renting anything. Most visitors never make it over there because they're focused on the Grotto.

That's worth knowing before you book, because Tobermory rewards people who plan a little. The Grotto and Flowerpot Island get the postcards, but they also get the crowds, and Bruce Peninsula National Park limits vehicle access to the busiest trailheads in peak season with a reservation system. If a national park day is the whole reason for the trip, sort that out before you sort out the cottage. Families with toddlers or anyone who'd rather skip a real hike should look at Singing Sands on Dorcas Bay instead, a calm, sandy, shallow alternative a short drive from town.

Divers and hikers get the most out of Tobermory, since it sits at the northern end of the Bruce Trail and the diving here (wrecks, caves, clear cold water) is genuinely some of the best freshwater diving anywhere. Day-trippers catching the Chi-Cheemaun to Manitoulin also use it as a jumping-off point.

Book early for July and August, both for the cottage and for any park reservations. September is the quiet-lover's window: the crowds thin out, the escarpment starts turning colour, and the lake is usually still warm enough to swim.

Insider tip: skip the parking crunch at the Grotto entirely by catching a water taxi from Little Tub Harbour straight to the trailhead, or just get there before 9am. Either way beats circling for a spot at noon.